(2Z,4E)-5-[(1S,3S,5S,8R)-3,5-dihydroxy-1,8-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

Details

• Internal ID: 4e8394ca-f912-4f6d-b6c5-baf08ebcc66b
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Medium-chain fatty acids
• IUPAC Name: (2Z,4E)-5-[(1S,3S,5S,8R)-3,5-dihydroxy-1,8-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid
• SMILES (Canonical): CC(=CC(=O)O)C=CC1(C2(CC(CC1(OC2)O)O)C)C
• SMILES (Isomeric): C/C(=C/C(=O)O)/C=C/[C@@]1([C@@]2(C[C@@H](C[C@@]1(OC2)O)O)C)C
• InChI: InChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-14(3)13(2)7-11(16)8-15(14,19)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-/t11-,13+,14+,15-/m0/s1
• InChI Key: HNRGNQMAJHAVCN-VSTJRZLJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.46
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9653	96.53%
Caco-2	+	0.7513	75.13%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6230	62.30%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.9618	96.18%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6533	65.33%
P-glycoprotein inhibitior	-	0.9544	95.44%
P-glycoprotein substrate	-	0.8038	80.38%
CYP3A4 substrate	+	0.5750	57.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8881	88.81%
CYP3A4 inhibition	-	0.8761	87.61%
CYP2C9 inhibition	-	0.8417	84.17%
CYP2C19 inhibition	-	0.8801	88.01%
CYP2D6 inhibition	-	0.9558	95.58%
CYP1A2 inhibition	-	0.8270	82.70%
CYP2C8 inhibition	-	0.8485	84.85%
CYP inhibitory promiscuity	-	0.9292	92.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5846	58.46%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.8920	89.20%
Skin irritation	-	0.5738	57.38%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7075	70.75%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8214	82.14%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5187	51.87%
Acute Oral Toxicity (c)	III	0.3757	37.57%
Estrogen receptor binding	+	0.7170	71.70%
Androgen receptor binding	+	0.5755	57.55%
Thyroid receptor binding	+	0.6332	63.32%
Glucocorticoid receptor binding	+	0.5985	59.85%
Aromatase binding	+	0.7553	75.53%
PPAR gamma	+	0.6223	62.23%
Honey bee toxicity	-	0.7992	79.92%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9812	98.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2061	P19793	Retinoid X receptor alpha	95.10%	91.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.86%	91.11%
CHEMBL1870	P28702	Retinoid X receptor beta	90.76%	95.00%
CHEMBL2004	P48443	Retinoid X receptor gamma	90.09%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.61%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	86.02%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.69%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.07%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.19%	94.45%

Plants that contains it

• Vigna unguiculata

Cross-Links

• PubChem: 162951248
• LOTUS: LTS0067811
• wikiData: Q105031026